Prerequisites A site with a course and an enrolled user. Setup outgoing email in your moodle instance. (For simplicity, you can use tools for testing outgoing emails such as Mailcatcher or MailHog). Log in as an admin. Go to " Site administration / Plugins / Filters / Manage filters " Enable "Display emoticons as images" Go to " Site administration / Plugins / Text editors / Atto HTML editor " Add " emoticon " at the end of the " insert " section of the " Toolbar config " field.  Save the changes. Testing scenario 1 Create a forum in the course. Set the subscription mode to 'Forced subscription'. Logout Log in as the student. Make a post. Log in as the admin and reply to the post with the following content checking 'Send forum post notifications with no editing-time delay'. :) :-D ;-) :-/ V-. :-P B-) ^-) 8-) :o) :( 8-. :-I :-X 8-o P-| 8-[ xx-P |-. }-] (h) (heart) (y) (n) (martin) ( ) Run cron. Verify the e-mail received does feature normally sized emojis.